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Anime and Manga
- Revy in Black Lagoon have clear white irises, to accentuate her inner turmoil.
- Whenever someone is emotionally broken in Elfen Lied (which is often) they get these, along with a Kubrick Stare.
- Just about everyone in the Hellsing manga.
- Solf J. Kimblee in a late chapter of Fullmetal Alchemist when he's telling Pride about how screams are soothing to him.
- A favorite shot of Magical Girl Lyrical Nanoha's resident Mad Scientist, Jail Scaglietti, when he's taunting the Time-Space Administration Bureau via broadcast.
- Higurashi: When They Cry has a lot of "emo-distortion" expressions, Mad Eye being just one of the effects. Rika busting this out in the second season is truly a sight to behold.
- Kurt Godel from Mahou Sensei Negima! (possible spoilers)
- Marik of Yu-Gi-Oh! did this from time to time, though he was crazy all the time, and this was because it was his dark side.
- The entire cast of Deadman Wonderland exhibits this, sometimes as their default expression. It fits, since most of them are clinically insane to some degree.
- Ryuga does this quite often in Metal Fight Beyblade. It succeeds in making him appear quite off his rocker (and he is).
- 86 from Vassalord has this as his default expression. And when 86 gets serious somehow his eyes get even more crazy looking!
- Chuck from Panty & Stocking with Garterbelt has one large white eye and a smaller black one.
- Tokyo Ghoul has two variations of this.
- Protagonist Kaneki Ken has one, as a result of being a Half-Human Hybrid. His right eye remains normal, but his left is prone to giving away his Ghoul nature. He frequently wears an eye-patch to conceal it. (It turns out to be a tell-tale sign of any Half-Human Hybrid, known as One-Eyed Ghouls.)
- Kureo Mado, a sadist CCG Investigator obsessed with killing Ghouls to produce new anti-Ghoul weapons, has one lazy eye and one that is almost always bulging.
- Johnny the Homicidal Maniac. Quite a lot of the time, really. But then, he's insane quite a lot of the time.
- Anything by Jhonen Vasquez has this.
- The Mask: ◊
- Falling under the "Deranged Character" subset are The Joker's eyes as drawn in Batman: RIP. There, one of his pupils is drawn slightly larger than the other, giving him a dangerous and mentally off-kilter look. The effect is so slight that it's only noticeable in close-up shots of the character, but it's definitely there. Then again, he is a Monster Clown with enough crazy to fill Arkham Asylum's halls ten times over.
- Most Returners in Dead Eyes Open seem to have one eye permanently open with a shrunken pupil.
- A specialty of Alan Davis. In the classic Detective Comics story "Fear for Sale", he combines this with an Expressive Mask.
Films — Animated
- In 9, 6 has one eye slightly larger than the other as a permanent feature, confirming his Cloudcuckoolander status.
- In An American Tail: Fievel Goes West, Wiley Burp teaches Tiger how to intimidate someone using "The Laaaayyyyzzzzyyy Eyyyyye!" which is essentially an intentional evocation of this trope.
Films — Live-Action
- In The New Guy, Luther teaches Dizzy his "Crazy Eye" which consists of squinting one eye and opening the other wide.
- Ragetti's wooden eye in Pirates of the Caribbean has this effect. It's too big for his socket, the wrong color, and always pointing away from his real eye. Many of Davy Jones' crewmen also have mismatched human and sea-creature eyes, notably Maccus the shark and Koleniko the puffer fish.
- The aptly-named Mad-Eye Moody from Harry Potter has a magical replacement eye. It's bright blue, the size of a golf-ball, has 360 rotation and can see through just about anything. It's also virtually never looking in the same direction as his other eye.
- The unnamed old man in Edgar Allan Poe's classic The Tell-Tale Heart. One eye, due to some deformity, is described as a "vulture eye" with a film over it. However, the eye drives the old man's roommate to insanity (whether this roommate is his servant, his apprentice, a caretaker or even his spouse is never mentioned).
- The Scarecrow from The Wonderful Wizard of Oz is described as having one eye larger than the other (accompanied by mismatched ears) due to poor artistry on his creator's part. He never really loses his cool at any point in the book, and he is never depicted as any more crazy than the rest of the Ozians, so it might be considered Subverted.
- The Red Right Hand of the mercurial Serial Killer Karkas in Galaxy of Fear is that he has one "crushed" eye.
- Scorpion Shards: Everyone maddened by Dillon gets one dilated pupil and one pinpoint pupil
Live Action TV
- Doctor Who:
- Roger Delgado's portrayal of the Master is very handsome and charming but has strikingly different eyes. One is always much wider than the other, which is unfocused and almost squinted. The effect is very disturbing.
- The Fourth Doctor's eyes do not quite ever point in the same direction, which is a really big part of how mad he looks. (The actor is perfectly capable of pointing both his eyes in the same direction when not in character.) His pupils are also noticeably off-centre.
- The Tenth Doctor also has slightly asymmetrical eyes. When one fan gave David Tennant's mother a painting they'd done of him with Self-Fanservice strongly averted, she commented that it was a bit boss-eyed, to which Tennant replied, "Face it, Mum, I am a bit boss-eyed."
- In The Invasion, Vaughn's right eye is half-closed through most of the serial, until he turns against the Cybermen; after that, it's wide open.
- Having a literal Mad Eye is Older Than Print: Cuchulain, the Irish folk hero. Whenever he went into one of his unstoppable rages, one of his eyes would get smaller and the other would get bigger. " ... he sucked one eye so deep into his head that a wild crane couldn't probe it onto his cheek out of the depths of his skull; the other eye fell out along his cheek." Now thats a Mad Eye.
- This guy: o_O
- Brian Pillman, after he became a loose cannon. Though it was more like madman with a lazy eye, rather than anything exaggerated.
- Cibernético has a split right pupil. And though he has had his bouts with madness, this is more a sign of, well, being a cyborg.
- Kane had one on Monday Night Raw after unmasking. One eye was an icier blue with a smaller pupil.
- Kzy of Dragon Gate seems to have the same affliction Kane does. More noticeable in fact because Kzy's other eye is brown.
- As seen in the National Wrestling Alliance, Wrestling Is, Chikara and such, Sinn Bodhi's right pupil tends to become an X.
- Cedric Pain in Reality OF Wrestling has a tiny left pupil.
- The Ghost Galaxy in Space Mountain: Ghost Galaxy has one skeletal-eye-socket and one giant blue nebula-eye.
- King K. Rool from the Donkey Kong Country game series.
- Earthworm Jim: Jim himself.
- In the re-render of Kingdom Hearts: Chain of Memories, Vexen gains one of these.
- Master Xehanort seems to have a rather nasty case of one in the 2.5 remix cover art.
- Laverne from Day of the Tentacle has one eye bigger than the other permanently. Which one depends on what side of her head you're looking at.
- Similarly, Doug Rattmann from the Portal games has one pupil permanently larger than the other. He's also a paranoid schizophrenic.
- Whenever Glottis from Grim Fandango gets excited about cars, or customizing something else with a motor or wheels, or gambling, he goes crazy-eyed, rapidly switching from one side to the other.
- In the Creepy and Cute pack for Spore, one of the added emotes (for the creepy side of things) is a version of this. Hilarity Ensues when your creature is covered entirely in eyes.
- In Nintendo World Cup, characters would get this when stunned by a tackle.
- Plants vs. Zombies:
- Crazy Dave. He's craaaaaazy.
- All the zombies in the game also have larger left eyes.
- The Strawburst plant in the second game has a staring right eye.
- For some reason, Liara in the Mass Effect series is often shown with one eye squinting slightly more than the other, prompting many a joke along this line.
- Chris Redfield on the cover of the original Resident Evil portrays this trope. Curse those zombie dogs.
- The Agents of Doom from Ratchet & Clank sport mismatched eyes, to go with their slasher smile and tendency to giggle.
- Incorporated into the designs of several of the animatronics from Five Nights at Freddy's. In the first game, Foxy has one normal eye under his eyepatch and one drooping eye; in the second, the Mangle has one eyeball and one tiny glowing light on each head.
- Black Mage, from 8-Bit Theater does this a lot, and was stuck for a while after a particular bit of frustration. As he put it after listening to one of Red Mage's "plans", "That's so stupid I can't even see straight."
- The titular amorph from Schlock Mercenary has one eye that is literally larger than the other, and the cartoonist is consistent about which is which, and what side each is on. Since Schlock can move his eyes around it doesn't really matter though.
- Several characters in Girl Genius do this sometimes... and there's one, a construct, who really does have one eye bigger than the other.
- Bob from Bob the Angry Flower. When Bob's scorching feral mania comes to the fore, he gets the Mad Eye.
- Vatsy, the insane journalist from Vatsy And Bruno, is always drawn with one eye in shadow to accentuate his wrong-ness.
- Helen Narbon of Narbonic gets this occasionally.
- Kano of Kagerou is frequently seen with pupils of very different sizes, though his actual eyes are the same size. The effect is halfway between Mad Eye and heterochromia.
- Nova from Keychain of Creation, especially when in Mad Scientist mode.
- Used in Commander Kitty to show intense pain, or to illustrate the sudden, terrifying feeling of being the Only Sane Man amongst a crazy crew that insists you get a costume change.
- In this El Goonish Shive sketchbook strip, Dan gets this while explaining his "master plan".
- Drowtales: One cameo character, Cac'bolg◊, has eyes like these. This emphasizes the fact that he's a member of Vel'Vloz'ress, the most messed up and chaotic faction in all of Chel'el'Sussoloth. Also, he seems to have some kind of obsession with poisons.
- Bubs, from Homestar Runner, definitely looks like this, but is no more crazy than the rest of the cast.
- The eponymous character from Spoilsbury Toast Boy has this permanently◊, as does his sister.
- Zero Punctuation will sometimes show these, usually of the Oh Crap! variety, having a character with one eye as a ring and the other as a circle.
- Nutty from Happy Tree Friends has this for both his eyes, each in a different variety: one with a constantly contracted pupil and one lazy green eye, the latter as a result of his sugar addiction. Interestingly, when he is cured in one episode, the differing colour remains while the lazy eye disappears, suggesting that part to be natural heterochromia rather than madness-related.
- Bumi from Avatar: The Last Airbender.
- Many characters from Invader Zim, including the titular invader on occasion.
- Mr. Demartino from Daria.
- Blitzwing from Transformers Animated has asymmetric eyes in one of his three faces. He's definitely crazy, having three personalities and all, but the odd-sized are on the most calm and calculating face. Really, it's mostly there to make it look like a monocle, as an homage to Colonel Klink.
- Shado the Brain Thief from Harvey Birdman, Attorney at Law. His mad eye alternates from right to left.
- Uncle Ruckus in The Boondocks (pictured at the top).
- The Tick — the title character, who is never entirely straight.
- Vince from Rex The Runt, one of the more random oddballs in claymation: given to random fits of Pavarotti and tangential one-word sentences.
- The starring spider in the (still unfinished) Art Institute of Portland student production Tangled Web, sometimes. Then again, he's decided to become a vegetarian and is desperate to avoid the delicious, delicious fly that's just landed in his web, so can you really blame him?
- The Vigar puppet on BRATS Of The Lost Nebula was the first one with different sized eyes to be approved by Brian Henson.
- VERY evident on Ed, Edd 'n' Eddy. "Boy Double D. Eddy never stares at ME like that."
- In The Critic, Duke Phillips once answered a reporter's question by telling him to "stare deep into the hypnotic powers of my EEEeeevil eeeye!" It apparently works.
- Discord of My Little Pony: Friendship Is Magic has red eyes with two irises of different sizes to illustrate his...discord!
- Two-Face gets this treatment as an effect of stylization in Batman: The Animated Series, as does Jonah Hex in the episode "Showdown." Characters that aren't completely human, such as Man-Bat and Clayface, sometimes do this.
- Dr. Mystico on Freakazoid!, as if his introductory speech weren't enough of a giveaway.
- Anisocoria, or asymmetric pupil dilation, can be a sign of serious neurological problems. This is also one of the first things EMTs and Paramedics check for when they suspect a concussion. Most carry penlights specifically to test this by shining it on the pupil and seeing it it reacts.
- It can also merely be a byproduct of severe past injury to the eye, such as with David Bowie, who owes his distinctively mismatched eyes to being nearly blinded in a childhood fight.